有機合成試薬「ＭＴ‐スルホン」の化学

Abstract

Here, the preparative reactions, chemical reactivities, and synthetic utilization of MT-sulfone, a typical dithioacetal S, S-dioxide, are described. MT-sulfone, which is the abbreviation name of (methylthio) methyl p-tolyl sulfone, is conveniently prepared from DMSO in the so-called “one-pot” manner. The combination of methylthio group and p-tolylsulfonyl (tosyl) group contributes to the easy formation of a carbanion and a radical on the central carbon of dithioacetal S, S-dioxide functionality and realizes many types of reaction that transform the dithioacetal S, S-dioxide group into the desired functionalities. The C-C bond formation of MT-sulfone with a wide range of functional groups such as alkyl halides, aldehydes, and carboxylic esters makes synthetic intermediates, which are finally converted to the desired target molecules. Thus, MT-sulfone has proven to be a versatile reagent in organic synthesis. In this review, the synthetic methods using the ketene dithioacetal S, S-dioxides that can be easily derived from MT-sulfone are also surveyed.